Real Estate Investment Properties for Sale in Longwood, FL

Looking for investment property in Longwood, FL with high ROI ?

Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Longwood, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3996 RADLEY COURT #3996 Longwood, FL Light and bright 2 bedroom, 2 bath condo in the highly desirable Wekiva Hunt Club communit...	2 beds \| 2 baths \| 1,427 sq.ft.	$270,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 3.27% Airbnb Rental Income: $1115 Traditional Rental Income: $1988 Airbnb ROI: -1.63% Traditional ROI: 3.27%
4102 CLUBSIDE DRIVE #4102 Longwood, FL Spacious 2-Bedroom Corner Unit in Clubside at Sabal Point â Private, Updated & Move-In R...	2 beds \| 3 baths \| 1,380 sq.ft.	$229,900	Airbnb cash on cash: -1.29% Traditional cash on cash: 4.01% Airbnb Rental Income: $1115 Traditional Rental Income: $1894 Airbnb ROI: -1.29% Traditional ROI: 4.01%
3235 WINDING PINE TRAIL Longwood, FL Life unfolds beautifully in this golf front estate in the desirable guard gated community ...	4 beds \| 6 baths \| 4,262 sq.ft.	$1,350,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.96% Airbnb Rental Income: $5377 Traditional Rental Income: $7787 Airbnb ROI: 1.18% Traditional ROI: 3.96%
211 FAIRWAY DRIVE #211 Longwood, FL Welcome to this charming condo located in the highly sought-after, gated community of The ...	3 beds \| 2 baths \| 1,496 sq.ft.	$187,500	Airbnb cash on cash: 7.73% Traditional cash on cash: 5.4% Airbnb Rental Income: $3221 Traditional Rental Income: $2080 Airbnb ROI: 7.73% Traditional ROI: 5.4%
204 TOMOKA TRAIL #204 Longwood, FL Stunning, Spacious Two-Story Condo in The Springs! Tucked away on the second floor of this...	2 beds \| 2 baths \| 1,599 sq.ft.	$245,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 5.25% Airbnb Rental Income: $1115 Traditional Rental Income: $2156 Airbnb ROI: -0.87% Traditional ROI: 5.25%
899 LORMANN CIRCLE Longwood, FL Welcome to your Longwood retreat. Enjoy the peace of mind that comes with no HOA! This me...	3 beds \| 2 baths \| 969 sq.ft.	$299,490	Airbnb cash on cash: 7.12% Traditional cash on cash: 4.66% Airbnb Rental Income: $3221 Traditional Rental Income: $1803 Airbnb ROI: 7.12% Traditional ROI: 4.66%
364 HOWARD BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bath home tu...	3 beds \| 2 baths \| 1,428 sq.ft.	$370,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.26% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.33% Traditional ROI: 4.26%
561 SHINING ARMOR LANE Longwood, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$358,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 2.71% Airbnb Rental Income: $2039 Traditional Rental Income: $1652 Airbnb ROI: 2.29% Traditional ROI: 2.71%
153 Duncan Trl Longwood, FL Property Highlights: (2024) NEW Architectural roof + gutters/guards. (2024) Full-Home PEX ...	3 beds \| 2 baths \| 2,596 sq.ft.	$539,900	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.57% Airbnb Rental Income: $3221 Traditional Rental Income: $2588 Airbnb ROI: 3.38% Traditional ROI: 3.57%
449 SPRINGWOOD COURT Longwood, FL Under contract-accepting backup offers. This beautifully updated three-bedroom, two-bath h...	3 beds \| 2 baths \| 1,075 sq.ft.	$317,500	Airbnb cash on cash: 5.99% Traditional cash on cash: 3.78% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.99% Traditional ROI: 3.78%
162 DUNCAN TRAIL Longwood, FL Under contract-accepting backup offers. Step into this updated 4-bed, 2-bath home that sit...	4 beds \| 2 baths \| 1,907 sq.ft.	$450,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 3.76% Airbnb Rental Income: $5377 Traditional Rental Income: $2468 Airbnb ROI: 8.09% Traditional ROI: 3.76%
230 HOWARD BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully updated 3-bedroom, 2-b...	3 beds \| 2 baths \| 1,173 sq.ft.	$262,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 5.43% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 7.54% Traditional ROI: 5.43%
731 CRESTBROOK LOOP Longwood, FL Welcome to 731 Crestbrook Loop in The Landings- one of Longwoodâs most desirable gated ...	3 beds \| 3 baths \| 2,140 sq.ft.	$405,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 6.05% Airbnb Rental Income: $3221 Traditional Rental Income: $3173 Airbnb ROI: 4.26% Traditional ROI: 6.05%
1889 RANCHLAND TRAIL Longwood, FL Exquisite 4-Bedroom Estate with Pool on 2+ Acres in the Coveted LongwoodâLake Mary Area,...	4 beds \| 3 baths \| 2,333 sq.ft.	$989,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.83% Airbnb Rental Income: $5377 Traditional Rental Income: $3252 Airbnb ROI: 2.96% Traditional ROI: 1.83%
4 WOODEN SHOE LANE Longwood, FL Under contract-accepting backup offers. Short Sale. Must See 4 bed, 2 bath home in the est...	4 beds \| 2 baths \| 2,682 sq.ft.	$350,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 5.03% Airbnb Rental Income: $5377 Traditional Rental Income: $2819 Airbnb ROI: 9.51% Traditional ROI: 5.03%
210 BANBURY COURT Longwood, FL New Improved Price! Your new pool home in the desirable Wekiva Hills community is waiting ...	4 beds \| 2 baths \| 2,720 sq.ft.	$450,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 6.28% Airbnb Rental Income: $5377 Traditional Rental Income: $3220 Airbnb ROI: 8.82% Traditional ROI: 6.28%
358 WINCHESTER COURT Longwood, FL Seller Motivated Closing cost, rate buy down incentives being offered or You can buy ...	3 beds \| 3 baths \| 1,682 sq.ft.	$319,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.78% Airbnb Rental Income: $3221 Traditional Rental Income: $2181 Airbnb ROI: 3.82% Traditional ROI: 2.78%
150 ESSEX DRIVE Longwood, FL Step into the warmth and charm of this rare cabin-style retreat nestled in the heart of Lo...	3 beds \| 2 baths \| 1,449 sq.ft.	$437,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 3.11% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.83% Traditional ROI: 3.11%
501 RIVERBEND BOULEVARD Longwood, FL Under contract-accepting backup offers. Are you ready to finally add the most important ke...	4 beds \| 2 baths \| 2,559 sq.ft.	$583,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 2.71% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 5.41% Traditional ROI: 2.71%
494 N PIN OAK PLACE #302 Longwood, FL Currently this unit is also available as a rental listing at $1,750. Resort-style livi...	2 beds \| 2 baths \| 1,110 sq.ft.	$199,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 6.41% Airbnb Rental Income: $1115 Traditional Rental Income: $1717 Airbnb ROI: 1.24% Traditional ROI: 6.41%
117 CROWN POINT CIR #5L Longwood, FL Welcome to Crown Point by the Springs in desirable Longwood. This charming ground-floor on...	1 beds \| 1 baths \| 728 sq.ft.	$140,000	Airbnb cash on cash: 4.11% Traditional cash on cash: 6.31% Airbnb Rental Income: $1304 Traditional Rental Income: $1193 Airbnb ROI: 4.11% Traditional ROI: 6.31%
448 VILLAGE VIEW LANE Longwood, FL Under contract-accepting backup offers. Step inside this beautifully upgraded Sabal Point ...	5 beds \| 3 baths \| 2,634 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $2938 Airbnb ROI: N/A Traditional ROI: 2.16%
674 PINE SHADOW COURT Longwood, FL Under contract-accepting backup offers. Discover this beautifully maintained 4-bedroom, 3-...	4 beds \| 3 baths \| 2,754 sq.ft.	$710,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.41% Airbnb Rental Income: $5377 Traditional Rental Income: $3403 Airbnb ROI: 4.75% Traditional ROI: 3.41%
2010 E Triangle Drive Longwood, FL Step Inside Your Future Home! This beautiful 3-bedroom, 2-bath, 1,684 sq ft home has been ...	3 beds \| 2 baths \| 1,684 sq.ft.	$349,900	Airbnb cash on cash: 5.36% Traditional cash on cash: 4.89% Airbnb Rental Income: $3221 Traditional Rental Income: $2342 Airbnb ROI: 5.36% Traditional ROI: 4.89%
470 S PIN OAK PLACE #312 Longwood, FL Bright, Updated Condo with Pond Views in A-Rated Seminole County School District! Welcome...	1 beds \| 1 baths \| 823 sq.ft.	$175,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.42% Airbnb Rental Income: $1304 Traditional Rental Income: $1352 Airbnb ROI: 0.69% Traditional ROI: 3.42%
851 N WAYMAN STREET Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully updated Longwood pool ...	3 beds \| 2 baths \| 1,353 sq.ft.	$360,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 4.89% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 5.88% Traditional ROI: 4.89%
430 BRASSIE DRIVE Longwood, FL This 4-bed 3 bathroom home in Longwood offers multi-generational flexibility, over 2,500 s...	4 beds \| 3 baths \| 2,537 sq.ft.	$550,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 4.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3177 Airbnb ROI: 6.78% Traditional ROI: 4.61%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 4.01% Airbnb Rental Income: $5377 Traditional Rental Income: $3213 Airbnb ROI: 6.54% Traditional ROI: 4.01%
1510 PELICAN STREET Longwood, FL Under contract-accepting backup offers. 3-bed, 2-bath residence nestled on a serene, tree-...	3 beds \| 2 baths \| 1,269 sq.ft.	$268,900	Airbnb cash on cash: 6.8% Traditional cash on cash: 4.74% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 6.8% Traditional ROI: 4.74%
556 LAKE WILDMERE COVE Longwood, FL MOTIVATED SELLER â MAJOR PRICE REDUCTION! Priced AGGRESSIVELY BELOW MARKET VALUE for an...	3 beds \| 3 baths \| 2,294 sq.ft.	$419,700	Airbnb cash on cash: 3.5% Traditional cash on cash: 4.09% Airbnb Rental Income: $3221 Traditional Rental Income: $2726 Airbnb ROI: 3.5% Traditional ROI: 4.09%
152 SPRINGWOOD CIRCLE #B Longwood, FL Updated and spacious condo on FIRST LEVEL close to community pool and laundry. 2 Bedrooms...	2 beds \| 1 baths \| 1,020 sq.ft.	$164,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 6.88% Airbnb Rental Income: $1115 Traditional Rental Income: $1512 Airbnb ROI: 1.97% Traditional ROI: 6.88%
1821 STANLEY STREET Longwood, FL Under contract-accepting backup offers. Welcome to this charming and spacious home tucked ...	3 beds \| 2 baths \| 2,567 sq.ft.	$485,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.53% Airbnb Rental Income: $3221 Traditional Rental Income: $2427 Airbnb ROI: 3.68% Traditional ROI: 3.53%
322 N SHADOWBAY BOULEVARD Longwood, FL Welcome to Lake Vista at Shadowbay - No HOA and No Restrictions! This beautiful and well-m...	3 beds \| 2 baths \| 1,599 sq.ft.	$525,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.25% Airbnb Rental Income: $3221 Traditional Rental Income: $2395 Airbnb ROI: 3.45% Traditional ROI: 3.25%
1581 MONICA JOY CIRCLE Longwood, FL Located in TOP RATED SEMINOLE COUNTY SCHOOL DISTRICT. Single story ranch home on a cul de ...	4 beds \| 2 baths \| 2,073 sq.ft.	$469,900	Airbnb cash on cash: 7.97% Traditional cash on cash: 4.04% Airbnb Rental Income: $5377 Traditional Rental Income: $2564 Airbnb ROI: 7.97% Traditional ROI: 4.04%
975 CROSS CUT WAY Longwood, FL Beautiful 4 bedroom 2.5 bathroom home Freshly Painted with Luxury Vinyl flooring and Stain...	4 beds \| 3 baths \| 2,289 sq.ft.	$470,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 4.19% Airbnb Rental Income: $5377 Traditional Rental Income: $2982 Airbnb ROI: 7.17% Traditional ROI: 4.19%
2330 PLEASANT DRIVE Longwood, FL One or more photo(s) has been virtually staged. Completely renovated and move-in ready, th...	3 beds \| 2 baths \| 1,311 sq.ft.	$395,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 5.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 5.04% Traditional ROI: 5.03%
116 WILD HOLLY LANE Longwood, FL Short Sale. This townhome offers incredible potential, featuring a versatile separate offi...	2 beds \| 2 baths \| 1,722 sq.ft.	$245,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 6.35% Airbnb Rental Income: $1115 Traditional Rental Income: $2329 Airbnb ROI: -0.51% Traditional ROI: 6.35%
721 ROCK CREEK LOOP Longwood, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 3 baths \| 1,998 sq.ft.	$390,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 4.79% Airbnb Rental Income: $3221 Traditional Rental Income: $2704 Airbnb ROI: 4.22% Traditional ROI: 4.79%
183 PARSONS ROAD Longwood, FL Escape into peace, nature and privacy on 12.3 acres of delightful Old Florida property. Wa...	4 beds \| 3 baths \| 3,731 sq.ft.	$5,800,000	Airbnb cash on cash: -0.49% Traditional cash on cash: -0.68% Airbnb Rental Income: $5377 Traditional Rental Income: $3288 Airbnb ROI: -0.49% Traditional ROI: -0.68%
3429 REGAL CREST DRIVE Longwood, FL Under contract-accepting backup offers. Timeless Elegance Meets Modern Luxury in the area'...	3 beds \| 3 baths \| 3,107 sq.ft.	$995,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2979 Airbnb ROI: 0.51% Traditional ROI: 1.03%

Real Estate investment in Longwood, FL

There are 120 properties for sale in the city of Longwood . The median list price in Longwood is $424,999 and the average price per square foot is $205. In January 2026, the average monthly cash on cash return in Longwood is 4.00%. The average monthly rental income in Longwood is $2,261.

Longwood, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 120 investment properties available for sale in Longwood.

In 2026, the best neighborhood to buy investment property is Longwood.

The ROI for Short-Term is higher than the Long-Term in Longwood with average rental income of $3,221.

Your search for investment property begins and ends here

Investment Property for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

2 beds | 2 baths | 1,427 sq.ft.

$270,000

Airbnb cash on cash: -1.63%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1115

Traditional Rental Income: $1988

Airbnb ROI: -1.63%

Traditional ROI: 3.27%

4102 CLUBSIDE DRIVE #4102

Longwood, FL

2 beds | 3 baths | 1,380 sq.ft.

$229,900

Airbnb cash on cash: -1.29%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $1115

Traditional Rental Income: $1894

Airbnb ROI: -1.29%

Traditional ROI: 4.01%

3235 WINDING PINE TRAIL

Longwood, FL

4 beds | 6 baths | 4,262 sq.ft.

$1,350,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $5377

Traditional Rental Income: $7787

Airbnb ROI: 1.18%

Traditional ROI: 3.96%

211 FAIRWAY DRIVE #211

Longwood, FL

3 beds | 2 baths | 1,496 sq.ft.

$187,500

Airbnb cash on cash: 7.73%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $3221

Traditional Rental Income: $2080

Airbnb ROI: 7.73%

Traditional ROI: 5.4%

204 TOMOKA TRAIL #204

Longwood, FL

2 beds | 2 baths | 1,599 sq.ft.

$245,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $1115

Traditional Rental Income: $2156

Airbnb ROI: -0.87%

Traditional ROI: 5.25%

899 LORMANN CIRCLE

Longwood, FL

3 beds | 2 baths | 969 sq.ft.

$299,490

Airbnb cash on cash: 7.12%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $3221

Traditional Rental Income: $1803

Airbnb ROI: 7.12%

Traditional ROI: 4.66%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,428 sq.ft.

$370,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $3221

Traditional Rental Income: $2122

Airbnb ROI: 5.33%

Traditional ROI: 4.26%

561 SHINING ARMOR LANE

Longwood, FL

N/A beds | N/A baths | N/A

$358,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $2039

Traditional Rental Income: $1652

Airbnb ROI: 2.29%